Patent GB-995363-A (GB)
Title: Monomeric and polymeric dye intermediates for use in colour photography
IPC: C07D231/52
Filed: 1962-05-24
Abstract: The invention comprises compounds of formula <FORM:0995363/C2/1> wherein Z is a hydrogen atom or a methyl group and Q is a radical, other than a phenolic or substituted phenolic radical, containing a colour-forming nucleus having as the active colour-forming group a structure of the formula (in its enol form) <FORM:0995363/C2/2> wherein <FORM:0995363/C2/3> or <FORM:0995363/C2/4> which yields upon oxidative colour coupling with a p-phenylene-diamine or p-aminophenol primary developing agent a quinoneimine, azomethine or azo dye.  The compounds are used to form addition copolymers with maleic acid derivatives (see Division C3) which are used in photographic compositions (see Division G2).  Compounds specified include those of formulae <FORM:0995363/C2/5> In examples: (1) phenyl-1-hydroxy-2-naphthoate is condensed with 2-aminoethyl vinyl ether to give 1-hydroxy-N-(b -vinyloxyethyl)-2-naphthamide; (2) 2-aminoethyl vinyl ether is condensed with p-(a -benzoylacetamido) benzenenelphonyl chloride to give p-(a -benzoylamino)-N - (b  - vinyloxyethyl) - benzenesulphonamide; (3) 1 - (4 - sulphophenyl) - 3 - methyl - 5 - pyrazolone is acylated with benzoyl chloride in the presence of potassium hydroxide and potassium carbonate to give the potassium salt of 1-(4-sulphophenyl) - 3 - methyl - 5 - benzyloxy - pyrazole which is treated with phosphorus pentachloride with cooling to give the corresponding sulphonyl chloride which is condensed with 2-aminoethyl vinyl ether; (4) 1-(p-chloroformylphenyl) - 3 - methyl - 5 - pyrazoyl ethyl carbonate is condensed with 2-aminoethyl vinyl ether. Specifications 527,283, 542,704, 600,023, 746,804, 747,801, 757,285, 765,893, 786,344, 786,345, 788,343 and 788,955 are referred to.ALSO:The invention comprises addition copolymers containing recurring structural units of a maleic acid derivative and also recurring structural units of formula <FORM:0995363/C3/1> wherein Z is hydrogen or methyl and Q is a radical other than a phenolic or substituted phenolic radical containing a colour-forming nucleus having as the active colour-forming group a structure of the formula (in its enol form) <FORM:0995363/C3/2> , wherein <FORM:0995363/C3/3> is <FORM:0995363/C3/4> or <FORM:0995363/C3/5> which yields upon oxidative colour coupling with a p-phenylene diamine or p-aminophenol primary developing agent a quinoneimine, azomethine or azo dye.  The copolymers are prepared by copolymerizing a monomer of formula <FORM:0995363/C3/6> wherein Z and Q are as defined above (see Division C2) with a maleic acid derivative.  The copolymers are used in photographic compositions (see Division G2).  In Examples: (1) 1 - hydroxy - N - (b  - vinyloxyethyl) - 2 - naphthamide (1 mole), maleic anhydride (1 mole) and azo-bis (isobutyronitrile) are refluxed in benzene to form the copolymer; (2) the copolymer formed in (1) is treated with n-butylamine to give the 1 : 1-copolymer of 1-hydroxy-N - (b  - vinyloxyethyl) - 2 - naphthamide and N-(n-butyl) maleamic acid and other half-ester and -amide derivatives are formed by reaction with diethylamine, n-octylamine, hexylamine, n-butanol and ethylene diamine (cross-linking); (3) p - (a  - benzoylacetamido) - N - (b  - vinyloxyethyl) - benzenesulphonamide or 1 - (4 - N - b  - vinyloxyethyl - sulphonamido - phenyl) - 3 - methyl - 5 - benzoyloxypyrazole or 1 - (4 - N-b -vinyloxyethyl - carbamyl - phenyl) - 3 - methyl - 5-pyrazolyl ethyl carbonate is copolymerized with maleic anhydride as in (1); (4) p-(a -benzoylacetamido) - N - (b - vinyloxyethyl) benzene sulphonamide is copolymerized with diethyl maleate. Specifications 527,283, 542,704, 600,023, 746,804, 747,801, 757,285, 765,893, 786,344, 786,345, 788,343 and 788,955 are referred to.